Fall in the Berkshires – 8 Reasons to Visit the Berkshires this Fall!

by Global Viewpoint
Fall in the Berkshires Massachusetts
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Why visit the Berkshires in the fall?

Considering a visit to the Berkshires in the fall? Autumn is the best time to visit the Berkshires, hands down. From leaf peeping and apple picking to country fairs and rustic farms, this region is among the best places to spend autumn in New England. It’s just a few hours from Boston and NYC, but you wouldn’t know it when you’re standing in this untouched autumn oasis.

If you’re looking to discover the best fall towns in New England, know that the Berkshires is home to several of them. Imagine rustic farms and charming homes decorated with pumpkins and mums. Picture yourself driving down winding country roads through untouched wilderness and idyllic lakes. This is the Berkshires in the fall (in a nut shell).

Last year was a Berkshires fall like no other
Last year was a Berkshires fall like no other

There are countless things to do in the Berkshires in the fall, including farm festivals, apple picking, outdoor water sports, and of course, leaf peeping. Add to that the fall flair of colorful leaves and crisp autumn air, and you’ll see why people from around the world come to experience a Berkshires fall.

As a native Bostonian, I’ve had the chance to explore the Berkshires during different seasons. The fall months are my favorite, by far, because of the reasons above. But why choose the Berkshires over other places in New England? Here are 8 compelling reasons why you should visit the Berkshires this fall!

For more New England Fall inspiration, follow my adventures on Instagram: @Global.Viewpoint

Fall in the Berkshires is a great time of year for traveling
Disclosure: This guide on fall in the Berkshires contains affiliate links, where I may receive commission at no extra cost to you

Best time to visit the Berkshires in the fall

Looking to figure out when to see the fall foliage in the Berkshires? You can’t go wrong with a visit from late September through early November. However, the best time for leaf peeping is typically the second and third week of October.

At higher elevations, you can expect peak foliage in the Berkshires to be between October 7-14 while the lower elevations reaches their peak between October 14-21. It’s important to note that “peak foliage” means that 70% of the leaves are changing, so you’ll still find beautiful trees outside of that narrow window.

Read next: When is the best time to visit New England

The Mohawk Trail in the Berkshires is an amazing place for leaf peeping
The Mohawk Trail in the Berkshires is an amazing place for leaf peeping

Looking to do a fall foliage road trip? Read next: Ultimate Guide to Fall in New England

1. Unspoiled nature and fun outdoor adventures

Located in scenic Western Massachusetts, the Berkshires is a hiker’s haven and a dilettante’s dream. During the autumn months, the entire region is bursting with intense fall foliage. Mountains and streams are covered by the flair of red and orange leaves – it’s a spectacular sight!

Perhaps one of the best vantage points is Massachusetts’ tallest mountain, Mount Greylock (3,489 ft.). From here, you can overlook 5 states on a clear day. In addition to the scenic drive up there, be sure to hike some of its trails along the Appalachian Trail.

Moreover, this time of year lends itself to exhilarating outdoor activities including kayaking, canoeing, and zip lining. One of my favorite memories from my recent trip was canoeing down the Housatonic River on a guided tour with Berkshire Canoe Tours. Hilary Bashara, who has owned this family-run tour for 20 years, is exceptionally knowledgeable and passionate about the local environment and community. It was wonderful paddling on a canoe, while learning about the wildlife and soaking in the fall ambiance around me.

Whether you’re an outdoor enthusiast or someone seeking a break from the hustle and bustle of the city, fall in the Berkshires will leave you in awe.

Read next: Top Hikes Across New England

Berkshire Canoe Tours is among the best nature excursions in the Berkshires
Berkshire Canoe Tours is among the top outdoor attractions in the Berkshires.

2. Classic New England towns in the Berkshires

Looking for where to stay in the Berkshires this fall? The Berkshires is home to countless rural towns, each with their own cozy inns, farms, and restaurants. Here are some of my favorite towns and villages to visit in the fall, including lodging options:

Lee, Massachusetts

A small village in Berkshire County known for its cozy B&Bs and quaint New England architecture. It’s located right on the Massachusetts Turnpike, making it a great location between Boston and New York.

The streets of Lee, MA in October
The streets of Lee, MA in October

Best places to stay in Lee:

Cheap: $Black Swan Lee
Mid: $$Chambery Inn
Luxury: $$$Devonfield Inn


Lenox is a top resort town in the Berkshires. It’s home to Tanglewood, an annual music festival as well as many outdoor adventure activities. It boasts thousands of acres of beautiful nature, including forests, meadows, and mountains. But on a rainy day, you can check out many museums and historic sites in town as well.

Lenox is a great town to visit in Western Massachusetts
Lenox is a great town to visit in Western Massachusetts

Best places to stay in Lenox, MA:

Cheap: $Yankee Inn
Mid: $$Seven Hills Inn
Luxury: $$$33 Main


For nature lovers, it doesn’t get much better than Pittsfield. This gorgeous fall town in the Berkshires is home to Pittsfield State Forest, which has over 11,000 acres of forest scenery and 30 miles of hiking trails. The town is also close to Hancock Shaker Village, one of the top hidden gems in New England.

Pittsfield is a top autumn destination in the Berkshires
Pittsfield is a top autumn destination in the Berkshires

Best places to stay in Pittsfield:

Cheap: $Berkshire Inn
Mid: $$Berkshire Mountain Lodge
Luxury: $$$Hotel on North

North Adams

North Adams is a cultural hub in the Berkshires that’s home to the Mass MoCA Museum and Boston Symphony Orchestra. It’s also right on Route 7 and Route 2 (Mohawk Trail), which are two of the best scenic drives in the Berkshires for leaf peeping.

Best places to stay in and around North Adams:

Cheap: $Maple Terrace Motel
Mid: $$The Porches Inn at Mass MoCA
Luxury: $$$The Lodge @ America’s Switzerland
Western MA comes alive in the autumn months
Western MA comes alive in the autumn months


From colonial-era inns to unique attractions like the Norman Rockwell Museum and Berkshire Theater Festival, Stockbridge is a top destination in Berkshire County. It’s super close to Lenox and Lee, making it one of the best places to stay in the Berkshires in the fall.

Best places to stay in Stockbridge, MA:

Cheap: $The Red Lion Inn
Mid: $$The Cottage B&B
Luxury: $$$The Inn at Stockbridge

Great Barrington

Located in the southern part of the Berkshires near Connecticut, Great Barrington is another great place to stay in the Berkshires for fall colors. It’s just a short drive to many beautiful spots, including Bash Bish Falls, Housatonic Flats Reserve, and Fountain Pond State Park. This makes it a gateway to the many nature destinations in the region.

Great Barrington is where you should stay in the Berkshires this fall
Great Barrington is where you should stay in the Berkshires this fall

Best places to stay in Great Barrington:

Cheap: $The Briarcliff Motel
Mid: $$Granville House
Luxury: $$$Wainwright Inn

3. Charming inns

In the Berkshires, you’ll find many warm and welcoming B&Bs that each have their own unique story, vibe, and décor. Among these intriguing guest houses, I was particularly impressed with the Harbour House Inn and Chambery Inn.

Harbour House Inn

Built in 1793, the Harbour House Inn is a historic, colonial-style home that embodies the charm of the Berkshires. Each of its 6 guest rooms offer an enchanting ambiance and all the amenities for a comfortable stay.

Each morning, the innkeeper, Jen Showalter, concocts a hearty gourmet breakfast using delicious local ingredients! One of my fondest memories from the Inn was spending breakfast conversing with fellow guests over interesting current events. Given our busy, hurried lifestyles, I feel that a friendly breakfast setting presents a wonderful opportunity to engage with our peers.

Harbour House Inn is one of the most historic houses in western Massachusetts
Harbour House Inn is a great place to spend during the fall months in the Berkshires.

Chambery Inn is another top place to stay in the Berkshires in the fall

Another inn that embodies the spirit of fall in the Berkshires is the Chambery Inn. Once a 19th-century schoolhouse, the Chambery Inn is a French-inspired B&B with 9 spacious suites. Each room is equipped with a fireplace and whirlpool tub, perfect for rest and relaxation!

One of my favorite experiences at the Chambery Inn was its homemade breakfast. Every morning, the innkeepers deliver a breakfast basket to each room— the best way to start the day.

Particularly during the stunning autumn months, each of these inns offer a unique lodging experience in the heart of the Berkshires!

Chambery Inn is one of the top hotels in the Berkshires
The Chambery Inn is another local favorite when visiting the Berkshires.

4. Captivating museums

On a rainy fall day in the Berkshires, you won’t have to twiddle your thumbs or risk water damaging your camera. Instead, hop into one of the region’s many museums and learn about the heritage behind this beautiful destination.

The Norman Rockwell Museum is a great rainy day activity during a visit to the Berkshires in the fall
The Norman Rockwell Museum is a great rainy day activity during a visit to the Berkshires in the fall

Top fall activities in the Berkshires for museum lovers

For those seeking a dose of art, culture, and history in their next vacation, look no further than the Berkshires! During my visit, I stopped by several museums that each had something special to offer. At the Norman Rockwell Museum, it was fascinating to learn about Norman Rockwell’s magnificent artwork and legacy on American history. From “The Four Freedoms” to “Home for Christmas”, Rockwell’s collection is truly an artistic inspiration.

It was also a pleasure checking out the Massachusetts Museum of Contemporary Arts (Mass MoCA) in North Adams. This factory-turned-art-museum is one of the largest contemporary art galleries in the United States. Much of the visual art on display is edgy and eccentric, which makes for a thought-provoking and unconventional experience.

My favorite museum of all is the Hancock Shaker Village in Pittsfield. Established in 1791, Hancock Shaker Village is a historic landmark and museum that offers a glimpse of the simple and rustic lifestyles of the Shakers. Similar to the Quakers, the Shakers were a Christian sect that passionately practiced pacifism, equality, and sustainability.

Inside this village, you’ll find historic buildings and artifacts, handicraft exhibitions, and farm animals that bring the Shaker community to life. Whether you’re planning a weekend trip or extended getaway to the Berkshires, make sure these museums are on your list!

Hancock Shaker Village is one of the top attractions in the Berkshires
Hancock Shaker Village is one of the top things to see and do in the Berkshires.

5. The Berkshires is praised for its farm-to-table dining.

What better way to experience a new place than through its food? With the autumn harvest in full swing, fall in the Berkshires is a great time to eat your way through its amazing restaurants.

After a long day exploring the fall foliage, it’s nice to stop by local restaurants and diners for a taste of the local cuisine. One thing that the Berkshires does extraordinarily well is farm-to-table dining. Many restaurants and B&Bs integrate locally-sourced ingredients into their menus, which come from the fall harvest. Cider donuts, anyone?

In particular, I was impressed by Trail House Kitchen in North Adams. Named after the nearby Appalachian and Mohawk trails, Trail House Kitchen is a family-run restaurant with a beautiful outdoor patio and delicious comfort food. My favorite dishes were the beef medallions and pomegranate cheesecake, which were truly out of this world!

In addition to trying dishes at local restaurants and cafes, I also made the obligatory stop to Chocolate Springs Café in Lenox. This confectionery shop is a chocolate lover’s dream. I’d even argue that it produces some of the finest chocolate in the world. As a self-proclaimed chocolate connoisseur, I was most impressed by the hot chocolate and passion fruit chocolate bars. After endless sightseeing in the Berkshires, a tasty treat is much needed.

Trail House Kitchen is one of the best restaurants in the Berkshires
Trail House Kitchen is a wonderful local restaurant in the Berkshires.

6. Country fairs and other special events

There’s always something exciting happening in the Berkshires, especially during the fall months.

Locals and visitors alike are drawn to the region for its festivals and fairs. Here are some of the popular ones you can’t miss:

North Adams Fall Foliage Parade: A day of family fun, including a children’s fair, road race, craft fair, and various performances.

Berkshire Botanical Garden Harvest Festival: One of the region’s largest autumn festivals. More than 100 artisan vendors are in attendance, in addition to families who come for the live entertainment, hay rides and games, and other farm-based activities. children’s activities.

Hancock Shaker Village Country Fair: A popular event where local farmers and artisans bring a festive fall atmosphere to this historic village.

Hawthorne Valley Fall Festival: A free public event brimming with live music, local food and artisan goods, apple cider pressing, and hay rides.

7. The Berkshires is home to a wellness retreat like no other

Are you into wellness retreats? The Berkshires is home to one of the coolest wellness resorts in the country, Miraval Berkshires. It’s an all-inclusive, where you can choose from hundreds of unique experiences, including meditation and yoga sessions, archery, obstacles courses, and spa visits. In the winter, you can even do cold immersion here, which is a huge plus for Wim Hoffers like myself.

Yoga studio inside this wellness resort
Yoga studio inside this wellness resort

After a long day of chasing the fall colors around the Berkshires, I can’t imagine a better place to relax and unwind. It’s truly one of the coolest retreat centers worldwide. Visiting Miraval is undoubtedly among the top things to do in the Berkshires in the fall.

Read next: Miraval Berkshires Resort Review

Berkshires in November is well-spent at the Miraval Berkshires
Berkshires in November is well-spent at the Miraval Berkshires

8. Relaxation and inspiration in the Berkshires

Aside from its activities and attractions, the Berkshires fosters a serene atmosphere perfect for relaxation.

As you’re gazing at the fall foliage and dramatic landscapes, it’s easy to disconnect from your otherwise busy lifestyle and live (and feel) in the moment. Feeling the cool, gentle breeze as the vibrant-colored leaves sway in the air. Waking up every morning to the smell of livestock and birds chirping. Taking a deep breath and feeling inspired by the stunning scenery. These are some of the surreal experiences that will draw you to the Berkshires, year after year.

Especially during the fall foliage season, you will feel enlivened by the natural beauty and deep serenity of the Berkshires.

  • Thinking about visiting the Berkshires? Check out Berkshires.org – your quintessential planning guide to ensure a wonderful stay in the Berkshires!
Where to stay in the Berkshires this fall
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Fall in the Berkshires – 5 Reasons to Visit the Berkshires This Fall! | The Berkshires Official Website October 22, 2018 - 15:45

[…] Just a 3-hour drive from Boston and NYC, the Berkshires of Western Massachusetts truly come alive during the autumn months. From fall foliage and charming inns to captivating art museums and exquisite farm-to-table dining, there are countless reasons to visit. Last week, I had the pleasure of exploring the Berkshires and experiencing its tight-knit community and natural serenity firsthand. During this adventure, I was captivated and inspired by the Berkshires’ eclectic character. I learned about its culture, history, and landscape, all while having the opportunity to relax and unwind. Here are 5 compelling reasons why you should visit the Berkshires this fall! Read more about the Berkshires. […]


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